I visited the Iberian Peninsula 13th May to 30th May 2015. I was preparing my travel for weeks before I was going there and I have had the same problems getting a host like in Italy and Spain. My planning was to stay longer in the Algarve and make a day or two in Alentejo (Évora), but Sintra – which was recommended me by my host in Loulé, was a great place, too.
I came from Spain (Sevilla) by bus and my route was:
Algarve: Faro – Loulé – Portimão – Silves
Greater Lisbon: Sintra – Lisbon
I like Portugal, Lisbon, Patel de Nata and selfies with friends ;-).
Seriously I like the Algarve, too and I am very happy about my hosts in Loulé and Lisbon. The hostel in Sintra was not bad either, even it was small and on a second floor, it was very clean. The historical city and the surroundings of Sintra are worth to visit. More about the trip and the pictures you can find here as well as from my second visit of the country in 2017 – a long stay, because I was working there for a while. Though I explored more of the country and even two of the belonging islands.